Litchfield County, CT Homes for Rent

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  $7,500 per month

  • 5 Beds
  • 4.5 Baths
  • 3,642 Sq Ft
  • House for Rent

  18 Old Sharon Rd, Sharon, CT 06069

  ~Fair Rising~ Experience the grandeur of the past with this exquisite 1790 classic Georgian Colonial, nestled on a private 21-acre sanctuary just minutes from the charming center of Sharon. As you approach the residence via the elegant circular drive, you are welcomed by the breathtaking beauty of the meticulously maintained grounds. This historic gem boasts 5 well-appointed bedrooms upstairs,

  Diana Bisselle William Pitt Sotheby's Int'l

  18 Old Sharon Rd, Sharon, CT 06069
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  /22

  $4,000 per month

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • House for Rent

  10 Sentry Hill Rd, Roxbury, CT 06783

  Upper three-bedroom, 2 bath now available from September 30, 2025. Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 3-bedroom, 2 bath home rests on five acres with a gentle stream running through it. State of the art chef's kitchen with

  Melinda Dubow Klemm Real Estate Inc

  10 Sentry Hill Rd, Roxbury, CT 06783
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  $8,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,354 Sq Ft
  • House for Rent

  74 Tanner Hill Rd, Warren, CT 06777

  A rare opportunity to experience daily enjoyment of what many call "the best view in town". For years local residents have flocked to the top of Tanner Hill Road for the best vantage point of Warren's 4th of July fireworks show, and that same postcard worthy scenery overlooking Lake Waramaug and Hopkins Vineyard can be admired from nearly every space in this charming Colonial home. Enter into the

  Matt McElhone William Pitt Sotheby's Int'l

  74 Tanner Hill Rd, Warren, CT 06777
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  $7,500 per month

  • 3 Beds
  • 3 Baths
  • 3,071 Sq Ft
  • House for Rent

  379 Lake Rd, Warren, CT 06777

  Avail thru May 15, 2025 @ $7,500 per month. This one of a kind Lake Waramaug property offers lake access with a dock and maintains complete privacy and tranquility on over 30 acres. The property features an antique barn, gracious lawns and is surrounded by land trust trails for hiking. It is situated just off the lake with a short level walk down the driveway to the dock and a short drive to the

  Stacey Matthews W. Raveis Lifestyles Realty

  379 Lake Rd, Warren, CT 06777
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  $22,500 per month

  • 6 Beds
  • 5 Baths
  • 3,450 Sq Ft
  • House for Rent

  321 W Shore Rd, New Preston Marble Dale, CT 06777

  Available Aug 1- Sept 15 at 22,500. Inquire about custom terms, more time or annual terms. Inquire for details about use of Luxury pontoon boat for cruising and waterskiing. Enjoy this chic and renovated home on glamorous Lake Waramaug. Walk across the street to the fabulous dock with spacious lake side lawn. Canoe is available for use. 6 bedrooms (3 en-suite) with plenty of room for guests and a

  Stacey Matthews W. Raveis Lifestyles Realty

  321 W Shore Rd, New Preston Marble Dale, CT 06777
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  $7,500 per month

  • 4 Beds
  • 2.5 Baths
  • 3,026 Sq Ft
  • House for Rent

  18 Bear Burrow Rd, Roxbury, CT 06783

  Charming barn-style home on 15.27 acres off quiet country road. Four bedrooms and two and one half baths. Open floor plan. Exposed timber. Double sided stone fireplace. French doors to rear patio. In ground pool and barrel sauna. The perfect summer retreat in the beautiful town of Roxbury. Available short term between September to May for $7,500 per month. Contact agent for availability. Just 90

  Maria Taylor Klemm Real Estate Inc

  18 Bear Burrow Rd, Roxbury, CT 06783
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  $13,000 per month

  • 4 Beds
  • 3 Baths
  • 2,167 Sq Ft
  • House for Rent

  Unlisted Address

  Charming Twin Lakes Lakefront Retreat Nestled along the serene shores of Washining Lake, this beautiful 4 bedroom, 3 bath home offers a tranquil retreat for those seeking relaxation and natural beauty. With its spacious interior and breathtaking views, this rental property promises an unforgettable experience. This lake home is the perfect place to create lasting memories. Whether you seek a

  TAMI REID Northwest CT Realty

  Unlisted Address
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  $18,900 per month

  • 4 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • House for Rent

  23 Painter Hill Rd, Roxbury, CT 06783

  Pristine hilltop art filled home with views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. Wood burning fireplace, vaulted master bedroom with balcony and private bath. Dine or relax on the flagstone terrace. Ping pong, trampoline, croquet, badminton, gas BBQ, fire pit, bikes and board games. SUMMER June - August $18,900/month; OFF-SEASON September -

  Peter Klemm Klemm Real Estate Inc

  23 Painter Hill Rd, Roxbury, CT 06783
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  $24,900 per month

  • 1 Bed
  • 2 Baths
  • 900 Sq Ft
  • House for Rent

  253 Tophet Rd, Roxbury, CT 06783

  Large Vaulted Pool House. King BR + BA,Trundle BR/BA - King Bed or 2 Twins. Chef's Kitchen. Covered BBQ. Deck Overlooking Pool.Garage. SUMMER June - August $24,900/month Memorial - Labor Day $59,000; OFF-SEASON September - May $10,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $129,000. Possible to rent with Main House with its own plunge pool. See listing for 253

  Peter Klemm Klemm Real Estate Inc

  253 Tophet Rd, Roxbury, CT 06783
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  $13,900 per month

  • 1 Bed
  • 1.5 Baths
  • 995 Sq Ft
  • House for Rent

  141 Melius Rd, Warren, CT 06754

  Comfortable One-Bedroom Cottage on Warren's best farm walking, running, bike riding road near Warren Town Center. Set on a 20-acre site. Older shared tennis court. Close to Mohawk Skiing, Lake Waramaug Town and State Beaches, Washington. Kent and Litchfield Restaurants.SUMMER June - August $13,900/month; Memorial - Labor Day $34,900;OFF-SEASON September - May $6,900/month. If over 3 months,

  Peter Klemm Klemm Real Estate Inc

  141 Melius Rd, Warren, CT 06754
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  $26,900 per month

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft
  • House for Rent

  143 Melius Rd, Warren, CT 06754

  Pristine barn-style home on scenic dirt road with stream and small ponds. Walk or bike ride along this scenic road into a land preserve and historic farms. Magnificent stone fireplace, vaulted beam living room. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea. Tennis. Close to Lake Waramaug and Mohawk Mountain Skiing. Main House:

  Peter Klemm Klemm Real Estate Inc

  143 Melius Rd, Warren, CT 06754
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  $24,900 per month

  • 3 Beds
  • 3.5 Baths
  • 1,469 Sq Ft
  • House for Rent

  253 Tophet Rd, Roxbury, CT 06783

  Restored 3-BR Victorian Cottage with pool/spa/hot tub with wonderful gas barbeque stone terraces. Best scenic road for walking or bike riding by historic farms and homes owned by numerous artists, authors, actors and Wall Street executives. Relax or dine poolside surrounded by hedges and blue hydrangea. Specimen trees, enough flowers to keep vases full. Large wood burning fireplace. SUMMER June -

  Peter Klemm Klemm Real Estate Inc

  253 Tophet Rd, Roxbury, CT 06783
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  $24,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  Unlisted Address

  Meander down the most scenic of Roxbury dirt roads to reach "Tunnel Road 4-BR" tucked between the Shepaug River, historic wood Judd's Bridge and Farm and 1000 acres of Steep Rock land trust with endless hiking trails. Pristine renovated private country home with year round 8'x 16' spa pool, wood burning fireplace and open floor plan. Dine or relax on the granite terrace or covered front porch.

  Peter Klemm Klemm Real Estate Inc

  Unlisted Address
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  $44,900 per month

  • 7 Beds
  • 9 Baths
  • 15,000 Sq Ft
  • House for Rent

  10 Sunny Ridge Rd, Washington, CT 06793

  Major estate with the highest standards of construction located within the Sunny Ridge historic district. Situated on 10 private, park-like acres with an over-sized heated pool, fabulous stonewalls, giant dining terraces, pond and orchard. 7+ bedrooms, Billiard room, screening room, paneled library, sunroom, new country kitchen, 100-person party room boasts a restaurant size bar, sound system and

  Peter Klemm Klemm Real Estate Inc

  10 Sunny Ridge Rd, Washington, CT 06793
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  $30,900 per month

  • 3 Beds
  • 3.5 Baths
  • 4,251 Sq Ft
  • House for Rent

  45 Moosehorn Rd, Roxbury, CT 06783

  Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns

  Peter Klemm Klemm Real Estate Inc

  45 Moosehorn Rd, Roxbury, CT 06783
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  $30,900 per month

  • 6 Beds
  • 3.5 Baths
  • 2,716 Sq Ft
  • House for Rent

  33 Sentry Hill Rd, Roxbury, CT 06783

  Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

  Peter Klemm Klemm Real Estate Inc

  33 Sentry Hill Rd, Roxbury, CT 06783
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  $30,900 per month

  • 4 Beds
  • 3 Baths
  • 3,530 Sq Ft
  • House for Rent

  51 Senff Rd, Washington, CT 06793

  Pristine 5-bedroom private home on scenic dirt road ideal for walking, jogging and biking. Magnificent design with 2 gas fireplaces and filled with the art of Thomas McKnight. 2 over-sized wood decks overlooking the heated pool surrounded by endless summer hydrangea and 3 acres of lawns. The perfect location minutes from the center of Washington, the Mayflower and Winrian Inns & Spas.SUMMER:June

  Peter Klemm Klemm Real Estate Inc

  51 Senff Rd, Washington, CT 06793
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  $26,900 per month

  • 4 Beds
  • 4 Baths
  • 2,396 Sq Ft
  • House for Rent

  247 Painter Hill Rd, Roxbury, CT 06783

  Mint St. Barth's-style home in perfect hilltop neighborhood with heated pool. Exceptional interior design with two wood burning fireplaces and vaulted ceilings. SUMMER June - August $26,900/month, Memorial - Labor Day $69,900. OFF-SEASON: September - May $12,900/month--If over 3 months, subtract $1,000 per month. And no tax is due. ANNUAL: $159,000. Inquire for other/shorter rental terms.

  Peter Klemm Klemm Real Estate Inc

  247 Painter Hill Rd, Roxbury, CT 06783
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  $26,900 per month

  • 4 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • House for Rent

  47 Calhoun St, Washington Depot, CT 06794

  Charming mint renovated Nantucket-style cottage set on 25 acres of meadows with apple trees and 200-year old maples. Breathtaking hilltop views overlook farms, the Town of Washington and church steeples. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.SUMMER June - August $26,900/month; Memorial - Labor Day $69,900; OFF-SEASON

  Peter Klemm Klemm Real Estate Inc

  47 Calhoun St, Washington Depot, CT 06794
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  $24,900 per month

  • 3 Beds
  • 3 Baths
  • 1,933 Sq Ft
  • House for Rent

  110 Shearer Rd, Washington, CT 06793

  Restored country cottage furnished with antiques, fine furnishings & oriental rugs. New gunite in-ground pool and terrace. Wonderful scenic dirt road walking or bike riding through historic estate neighborhood. Relax or dine with a bbq on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.SUMMER June - August $24,900/month; Memorial - Labor Day

  Peter Klemm Klemm Real Estate Inc

  110 Shearer Rd, Washington, CT 06793
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  $15,900 per month

  • 2 Beds
  • 2 Baths
  • 2,153 Sq Ft
  • House for Rent

  17 Kirby Rd, Washington, CT 06793

  Pristine Arts & Crafts Carriage House. Perfect setting on Washington's Historic Green surrounded by the Frederick Gunn School and historic shingle-style Rossiter mansions. Ground floor ensuite primary bedroom, office with sleeper sofa and cozy den with wood-burning fireplace. Upstairs, king bedroom with ensuite bath, large living room, dining room and eat-in kitchen. Fabulous mahogany deck for

  Peter Klemm Klemm Real Estate Inc

  17 Kirby Rd, Washington, CT 06793

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